Ethyl cyanoacetate → Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

HRID 27686

반응식

HRID 27686 반응식
[Na].[C:2]1([N:8]=[N+:9]=[N-:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)C.O>[NH2:12][C:11]1[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

6

반응물 3

HCID 7764Ethyl cyanoacetateHCID 69319AzidobenzeneHCID 5360545Sodium

생성물 1

HCID 253349Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

A solution of sodium (2.04 g; 0.089 mole) in ethanol (50 ml) was added to a mixture of phenyl azide (11.9 g; 0.1 mole) and ethyl cyanoacetate (11.3 g; 0.1 mole) and the product gently warmed to 45° C. with stirring for 5 mins. After stirring at ambient temperature for a further 15 minutes the flask was immersed in water at room temperature for 3 hrs. A white solid separated which was filtered off after dilution of the mixture with water and washed with water. Recrystallisation from ethanol gave 18.4 g. (79%) of material of mp 124.5-125.5° C. (lit mp 126°; B. R. Brown, D. L. Hammick and S. G. Heritage J. Chem. Soc. 3820 [1953]).

후처리

  1. stirringAfter stirring at ambient temperature for a further 15 minutes the flask
  2. customA white solid separated which
  3. filtrationwas filtered off after dilution of the mixture with water
  4. washwashed with water
  5. customRecrystallisation from ethanol
  6. customgave 18.4 g

출처 및 근거

ORD 기록
ord-b3e067cf1f534ffe8363abbafa8f7d65
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223032

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